I have jail broken/rooted/unlocked/whatever_term_they_come_up a lot of devices: iPhones, Windows Mobile and Android phones, PS3s, PSPs, XBOXes, a Blackberry as far as I can remember and maybe some more. All that my friends and family threw at me "got under the knife".

Never had the guts to jailbreak, I'm pretty sure I'd find it to be a hassle every time a new update comes out......Rather pay for things I like/need and have them work and be taken care of by someone else =)

There is certainly a trade off to jailbreaking. Some say it isn't worth the hassle. I equate it to the equivalent of a standard consumer vs a power user in the PC market. Windows users that love to play with everything under the hood as opposed to those who just want to install programs and have it all just work.

I do love to play with everything under the hood and all the jail break features do tempt me so much, but I am a scaredy cat

Just read this now. As far as I am aware, it is pretty much impossible to brick an apple device jail breaking it. The jailbreak doesn't touch the core firmware of the device, just the operating system. The worse that can happen is that you will have to do a restore and lose everything that was stored on the device.

I managed to un-jailbreak my I Phone by updating to iOS 5.0 .
After that i managed to jailbreak it but got a No Service warning !
Re un-jailbreak , downgraded to iOS 4.3.5 , jailbreak tethered ! Now i am stuck ! The phone its working just fine , the problem is the need to connect my phone to a computer everytime i run out of battery or i shut my phone off just for booting my device!

Tried to downgrade to iOS 4.3.3 for a untethered boot jailbreak , but i cant , because i keep getting some stupid errors !